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Vanilla Ice is back with a brand new invention: ‘That’s My Boy’

From Bob Barker in "Happy Gilmore" (1996) to Billy Idol in "The Wedding Singer" (1998), Adam Sandler has made a hilarious habit of highly unlikely cameos in his films. However, Sandler may very well have topped himself with the inclusion of the one and only Vanilla Ice in "That's My Boy," opening this Friday, June 15.

Though Vanilla Ice, aka Rob Van Winkle, plays himself in the film, to call the part a cameo is really an injustice. The poster-boy for early 90's fashion faux-pas plays an integral part in the R-rated comedy, which stars Sandler as a washed-up child star, Donny Berger, who became famous for having a son, Han Solo, with his older (and hotter) middle school teacher. Han, played by Andy Samberg, grew up awkwardly, changed his name to Todd, disassociated himself from his terrible father, and got engaged to Cape Cod catch, Jamie (Leighton Meester).

To reconnect with his son, Donny calls on the help of his good buddy Vanilla Ice. And honestly, what could be funnier than that? When you think of the early 90's white rapper, with his zigzag hairdo and his Z-Cavaricci pants, I implore you not to snicker -- which is likely what Sandler had in mind when he cast Rob.

But while many cameos are worth laughing at, Ice is perfectly comfortable laughing along with us. When I spoke to him at the junket for the film, I found a man extremely comfortable in his own skin, quick to laugh, and proud of where he's been. When I asked him where he found that pride, his answer was downright philosophical: "Why am I hating on all this? This is the best thing that ever happened. We are who we are because of who we were."

We haven't heard much from Ice since he sold over 11 million copies of his 1990 debut album, "To the Extreme." But with his role in "That's My Boy," Ice may very well be back. His real-estate reality show "The Vanilla Ice Project" is a DIY channel staple, he released an album last year, and he may have have found a future musical partner with a lot of pull: Sandler himself. When I asked Ice about a possible musical collaboration between he and the man who performed the greatest Hanukkah song ever, Ice smiled his infectious grin, and told me to "wait and see."

Insider access with Vanilla Ice and the rest of the 'That's My Boy' cast: